My First Time With TS

This a true accounting of the first time I was with a Tgirl. There have been many since, but this will always be my favourite encounter.

I used to work up in northern Alberta years ago. The schedule was one week in and one week out. Shift change was always on the Wednesday. So on Wednesday morning I would pack up and head to work at about 5 am. I would roll into work between 11 to 11:30 am and start my week. The next Wednesday I would be all packed up and heading home to Calgary by about 12:30 pm.

The trip could always take me around Edmonton but I usually passed through Edmonton to make a stop at a Massage Parlour or maybe see what girls were on the street that looked inviting. This one particular trip I saw this amazing looking girl standing on one of the regular stroll streets. She was dressed in jeans and a sort of western shirt. She reminded me of the girls you see in the barrel riding at the rodeo. She had long brunette hair, tanned complexion, slender and a great smile. I circled around and she was still there so I stopped and she hopped in and I pulled away.

We had the usual conversation, you know, are you a cop? How much? You know the routine. We agreed on a donation and headed to her place. Not the usual routine for a street lady who usually have a hotel room or some little secret spot to park. We went to her townhouse in the NE of Edmonton.

During the trip we had some light conversation, you know, the weather, exchanging names, a little small talk. I could not help but notice she was giving me some pretty strange looks, like she was sizing me up, trying to figure me out. It was kind of weird but I did not let it deter me. She was hot, had a sexy voice, and I was already anticipating some hot sex.

We arrived at her place and went in. She said she would be right back; she wanted to slip into something more comfortable. She told me to get comfortable myself which I took as get naked so I did. On her way up the stairs she had stopped and turned on her TV and started a VCR playing (yes, this is per-dvd days). Once naked I looked up to see what was playing on the TV and low and behold there was this hot looking girl leaning back in a limo receiving some face from a guy. When the camera zoomed in he was not licking pussy, but sucking cock. I was like holy shit! Never had I seen anything like that before. Now I am not naive or anything, I was well aware of transvestites and shemales, just never actually seen one in video.

Well a few moments later this lovely girl comes down the stairs and is dressed in a sexy white baby-doll, garter and nylons. I was very impressed and aroused. She looks at the TV and then at me. Looking back at the TV she says that the t-girl in the video is a friend of hers and asked if I was okay with the video. Sure I said, it did not bother me. Good she says, and then sits down beside me and we start kissing and she is playing with my dick. It’s not long before she is bending down and licking and sucking my cock. I start to play with her boobs and it is not long before the baby-doll is off. I do some booby sucking, lick, and fondling. She then does this amazing thing where she squeezes her nipple and some milk appears. Not a lot, just a small dribble. I lick it off.

She has this really nice fur rug in front of her fireplace and we move to there and continue with our fun. We continue with more kissing, fondling, groping, sucking and caressing. She then says that she needs me inside her. At this point her panties come off and there it is, a cock. I had no idea until that very moment she had one, it was an amazing tuck job to be sure. I kind of stared at it and she gets this worried look on her face and asked if I was okay. Sure, you just took me by surprise. She asks me if I am okay with it. I think for a moment. I am a pretty open minded guy. I would even call myself adventurous. I reach out and gently wrapped my hand around her cock. I had never touched a cock before, well except my own. It was already half erect and putting my little guy to shame. I said sure, I am okay with it.

She then puts a hat on my little guy and lowers herself onto it. As she is bouncing up and down on my cock I was totally mesmerized by her cock and how it moved. I suddenly had a new fascination. She kept riding me cowgirl until I was getting ready to pop, then she hopped off. The hat came off and she started to suck me off again. We were almost in a sixty-nine position, her hard as rock cock almost in my face and dripping pre-cum. I could not help myself; I had to have a taste so I took the head of her cock in my mouth and cleaned the pre-cum off. It was not a bad taste as I had feared. As I was about to cum I warned her and she let go of my cock with her mouth and I shot my load all over my belly. She got on her knees beside me and stroked herself until her seed spilled out and mingled with mine.

She then told me not to move and went and got a towel to clean up with. When that was complete she snuggled in and asked me how it was. I have never had a BJ (up to that point anyway) as good as she just gave me and it was the first time I had ever done greek. I told her awesome, and that I had a great time. I thanked her and she thanked me for not freaking out or doing something more extreme.

I left her place and continued on my way back home.

That was my very first time with a T-girl and though I did not do much more than take her in my mouth for a couple moments, and hold her cock for a few seconds, I was totally fascinated by her cock. That translated to cock in general. I have not met a t-girl since with as big a cock as her’s and I have seen some with pretty big cocks.

After much soul searching over the next couple months I decided I had to try to see her again. Never could find her on that street so I pretty much gave up. I decided to call a t-girl escort that was in the Edmonton Sun. I rented a hotel room and made the call. Set up an appointment with the t-girl (Zena I believe she went by). When she arrived I was surprised to find it was my girl from the street. Needless to say it was another great experience. This time I did more than the last time and I really enjoyed her cumming on my face as I brought her to climax sucking her off.

Sadly, I have never seen her again. Don’t know what happened to her. If she is here and remembers me, not likely as this is 19 years ago, I want to thank her broadening my horizons.

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